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Saving copy of the {{chembox}} taken from revid 440306455 of page 2-Aminopyridine for the Chem/Drugbox validation project (updated: '').
 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:2-Aminopyridine|oldid=440306455}} 440306455] of page [[2-Aminopyridine]] with values updated to verified values.}}
{{Chembox
{{Chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 410134784
| verifiedrevid = 477212553
| ImageFile = 2-aminopyridine.svg
| ImageFile = 2-aminopyridine.svg
| ImageSize = 120px
| ImageSize = 120px
| IUPACName = Pyridin-2-amine
| PIN = Pyridin-2-amine
| OtherNames = 2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine
| OtherNames = 2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine; α-Pyridylamine<ref name=NIOSH/>
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10008
| ChemSpiderID = 10008
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 21619
| ChEMBL = 21619
| EC_number = 207-988-4
| RTECS = US1575000
| UNNumber = 2671
| UNII = WSX981HEWU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
| StdInChI = 1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
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| SMILES = n1ccccc1N
| SMILES = n1ccccc1N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=5|H=6|N=2
| C=5 | H=6 | N=2
| Appearance = colourless solid
| Appearance = colourless solid
| Density =
| Density =
| MeltingPt = 59-60 °C
| MeltingPtC = 59 to 60
| MeltingPt_notes =
| BoilingPt = 210 °C
| Solubility = }}
| BoilingPtC = 210
| BoilingPt_notes =
| Section3 = {{Chembox Hazards
| Solubility = >100%<ref name=NIOSH/>
}}
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPtF = 154<ref name=NIOSH/>
| FlashPt =
| Autoignition = }}
| AutoignitionPt =
| PEL = TWA 0.5 ppm (2 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0026}}</ref>
| REL = TWA 0.5 ppm (2 mg/m<sup>3</sup>)<ref name=NIOSH/>
| IDLH = 5 ppm<ref name=NIOSH/>
| LD50 = 200 mg/kg (rat, oral)<br/>50 mg/kg (mouse, oral)<ref>{{IDLH|504290|2-Aminopyridine}}</ref>
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|311|312|315|319|335|411}}
| PPhrases = {{P-phrases|261|264|270|271|273|280|301+310|302+352|304+340|305+351+338|312|321|322|330|332+313|337+313|361|362|363|391|403+233|405|501}}
}}
}}
}}

'''2-Aminopyridine''' is an [[organic compound]] with the formula H<sub>2</sub>NC<sub>5</sub>H<sub>4</sub>N. It is one of three [[isomer]]ic aminopyridines. It is a colourless solid that is used in the production of the drugs [[piroxicam]], [[sulfapyridine]], [[tenoxicam]], and [[tripelennamine]]. It is produced by the reaction of [[sodium amide]] with [[pyridine]], the [[Chichibabin reaction]].<ref name=Ullmann>{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}</ref>

==Structure==
Although [[2-hydroxypyridine]] converts significantly to the pyridone [[tautomer]], the related imine tautomer (HNC<sub>5</sub>H<sub>4</sub>NH) is less important for 2-aminopyridine.

==Toxicity==
The acute toxicity is indicated by the [[LD50]] = 200 mg/kg (rat, oral).

==References==
<references/>

==External links==
* [https://web.archive.org/web/20110707111912/http://www.alkalimetals.com/msds/2-AMINOPYRIDINE_MSDS.pdf MSDS]
* [https://www.cdc.gov/niosh/npg/npgd0026.html CDC - NIOSH Pocket Guide to Chemical Hazards - 2-Aminopyridine]

{{DEFAULTSORT:Aminopyridine, 2-}}

[[Category:2-Aminopyridines]]